合成路线:The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III),which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV).This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V),which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII).The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII),which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX).Finally,this compound is reduced with NaBH4 in ethanol.
参考文献标题:
文献作者:Caldwell,A.G.; Whittaker,N.
参考来源:US 4204068
合成路线:The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III),which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV).This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V),which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII).The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII),which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX).Finally,this compound is reduced with NaBH4 in ethanol.
参考文献标题:
文献作者:Caldwell,A.G.; Whittaker,N.
参考来源:BE 0876670
合成路线:The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III),which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV).This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V),which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII).The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII),which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX).Finally,this compound is reduced with NaBH4 in ethanol.
参考文献标题:Hydantoin prostaglandin analog,potemt and selective inhibitors of platelet aggregation
文献作者:Harris,C.J.; Stepney,R.; Caldwell,A.G.; Whittaker,N.
参考来源:J Chem Soc Chem Commun 1979,(13),561-562
合成路线:The condensation of diethyl acetamidomalonate (I) with ethyl 7-bromoheptanoate (II) by means of sodium ethoxide in refluxing ethanol gives diethyl acetamido-(6-ethoxycarbonylhexyl)malonate (III),which is hydrolyzed and decarboxylated with refluxing concentrated HCl yielding 2-aminononanedioic acid (IV).This acid is esterified with SOCl2 and ethanol to the corresponding diethyl ester (V),which is condensed with vinyl cyclohexyl ketone (VI) to afford diethyl 2-[(3-oxo-3-cyclohexylpropyl)amino]nonanedioate (VII).The reaction of (VII) with potassium cyanate in ethanol-HCl gives the corresponding hydantoic ester (VIII),which is cyclized by heating at 100 C affording 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-oxopropyl)hydantoin (IX).Finally,this compound is reduced with NaBH4 in ethanol.
参考文献标题:Heterocyclic prostaglandin analogs.Part 2.Hydantoins and other imidazole analogs
文献作者:Whittaker,N.; Harris,C.J.; Stepney,R.; Caldwell,A.G.
参考来源:J Chem Soc - Perkins Trans I 1980,1(2),495-505
产品链接: CAS No.72814-32-5››